Furazolidone

Furazolidone

Systematic (IUPAC) name
3-{[(5-nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Legal status	?
Routes	Oral-Local
Identifiers
CAS number	67-45-8 Y
ATC code	G01AX06 QJ01XE90
PubChem	CID 3435
DrugBank	DB00614
ChemSpider	3317 Y
UNII	5J9CPU3RE0 Y
KEGG	C07999 N
ChEMBL	CHEMBL1103 N
Chemical data
Formula	C8H7N3O5
Mol. mass	225.16
SMILES [O-][N+](=O)c2oc(C=NN1C(=O)OCC1)cc2
InChI InChI=1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2 Y Key:PLHJDBGFXBMTGZ-UHFFFAOYSA-N Y
N (what is this?)  (verify)

Furazolidone is a nitrofuran antibacterial. It is marketed by Roberts Laboratories under the brand name Furoxone and by GlaxoSmithKline as Dependal-M.

Uses

Furazolidone has been used in human and veterinary medicine. It has a broad spectrum of activity being active against

• Gram positive
  • Clostridium perfringens
  • Corynebacterium pyogenes
  • Streptococci
  • Staphylococci
• Gram negative
  • Escherichia coli
  • Salmonella dublin
  • Salmonella typhimurium
• Protozoa
  • Giardia lamblia
  • Eimeria species
  • Histomonas meleagridis

Use in humans

In humans it has used to treat diarrhoea and enteritis caused by bacteria or protozoan infections. It has been used to treat traveler's diarrhoea, cholera and bacteremic salmonellosis. Use in treating Helicobacter pylori infections has also been proposed.^[1]

Furazolidone is also used for giardiasis (due to Giardia lamblia), though it is not a first line treatment.^[2]

As for all medicines the most recent local recommendations for its use should be always be followed. The usual dose is:

• Adult: 100 mg 4 times daily. Usual duration: 2-5 days, up to 7 days in some patients or 10 days for giardiasis.
• Child: 1.25 mg/kg 4 times daily, usually given for 2-5 days or up to 10 days for giardiasis.

Use in animals

As a veterinary medicine, furazolidone has been used with some success to treat salmonids for Myxobolus cerebralis infections.

It has also been used in aquaculture.^[3]

Use in laboratory

It is used to differentiate micrococci and staphylococci.

Mechanism

It is believed to work by crosslinking of DNA.^[4]

Side effects

Furazolidone is no longer available in the US. Though an effective antibiotic when all others fail, against extremely drug resistant infections, it has many side effects, and as with other nitrofurans generally, minimum inhibitory concentrations also produce systemic toxicity (tremors, convulsions, peripheral neuritis, gastrointestinal disturbances, depression of spermatogenesis.) Nitrofurans are recognized by FDA as mutagens/carcinogens, and can no longer be used since 1991.^[5]

References